N-(3-Eth-oxy-phen-yl)-4-methyl-benzene-sulfonamide.

In the title compound, C(15)H(17)NO(3)S, the two aromatic rings make a dihedral angle of 69.42 (9)° with each other and the bridging C-N-S-C torsion angle is 65.76 (16)°. Weak intra-molecular C-H⋯O inter-actions may affect the mol-ecular conformation. Two neighbouring mol-ecules generate a hydrogen-bonded dimer about a center of inversion through a pair of inter-molecular N-H⋯O inter-actions, forming an R(2) (2)(8) ring motif. Furthermore, two inter-molecular C-H⋯π inter-actions contribute to the stability of the crystal packing.

Related literature

For the biological activity of sulfonamides, see: Berredjem et al. (2000 ▶); Lee & Lee (2002 ▶); Soledade et al. (2006 ▶); Xiao & Timberlake (2000 ▶).

Experimental

Crystal data

C15H17NO3S

M = 291.37

Monoclinic,

a = 8.4612 (3) Å

b = 13.1862 (5) Å

c = 13.4237 (4) Å

β = 99.326 (2)°

V = 1477.90 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.34 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

13221 measured reflections

3608 independent reflections

2532 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.118

S = 1.00

3608 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022427/sj5019sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022427/sj5019Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H17NO3S	F(000) = 616
Mr = 291.37	Dx = 1.309 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4223 reflections
a = 8.4612 (3) Å	θ = 2.9–26.1°
b = 13.1862 (5) Å	µ = 0.23 mm−1
c = 13.4237 (4) Å	T = 296 K
β = 99.326 (2)°	Needle, colourless
V = 1477.90 (9) Å3	0.34 × 0.18 × 0.16 mm
Z = 4

Bruker APEXII CCD diffractometer	2532 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.036
graphite	θmax = 28.3°, θmin = 3.4°
φ and ω scans	h = −11→11
13221 measured reflections	k = −17→15
3608 independent reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0564P)2 + 0.2791P] where P = (Fo2 + 2Fc2)/3
3608 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.31 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.26616 (5)	0.52544 (3)	0.38686 (3)	0.0408 (1)
O1	0.17864 (15)	0.57574 (10)	0.30139 (9)	0.0518 (4)
O2	0.32376 (14)	0.58201 (9)	0.47639 (9)	0.0495 (4)
O3	0.30011 (17)	0.42300 (12)	−0.00035 (9)	0.0653 (5)
N1	0.42808 (16)	0.47848 (12)	0.35383 (11)	0.0439 (5)
C1	−0.1104 (3)	0.1674 (2)	0.4986 (2)	0.1033 (13)
C2	−0.0197 (2)	0.25798 (16)	0.47044 (18)	0.0623 (7)
C3	0.0767 (2)	0.31285 (17)	0.54323 (16)	0.0639 (8)
C4	0.1627 (2)	0.39529 (15)	0.51876 (14)	0.0532 (6)
C5	0.15151 (18)	0.42365 (13)	0.41926 (13)	0.0414 (5)
C6	0.0547 (2)	0.37042 (16)	0.34460 (15)	0.0562 (7)
C7	−0.0295 (2)	0.28784 (18)	0.37117 (18)	0.0673 (8)
C8	0.43243 (18)	0.41644 (13)	0.26721 (12)	0.0402 (5)
C9	0.5253 (2)	0.32988 (15)	0.28030 (15)	0.0548 (6)
C10	0.5428 (3)	0.27331 (17)	0.19682 (16)	0.0668 (8)
C11	0.4705 (2)	0.30085 (16)	0.10134 (15)	0.0591 (7)
C12	0.3773 (2)	0.38714 (15)	0.08949 (13)	0.0484 (6)
C13	0.3581 (2)	0.44493 (14)	0.17269 (13)	0.0466 (5)
C14	0.3347 (3)	0.37772 (18)	−0.09048 (13)	0.0624 (7)
C15	0.2431 (3)	0.4353 (2)	−0.17758 (16)	0.0836 (9)
H1A	−0.20100	0.15520	0.44690	0.1550*
H1B	−0.14680	0.18010	0.56160	0.1550*
H1C	−0.04160	0.10910	0.50520	0.1550*
H1N	0.486 (2)	0.4612 (14)	0.4062 (12)	0.0530*
H3	0.08400	0.29390	0.61060	0.0770*
H4	0.22780	0.43140	0.56900	0.0640*
H6	0.04630	0.38990	0.27740	0.0670*
H7	−0.09440	0.25150	0.32100	0.0810*
H9	0.57500	0.31030	0.34430	0.0660*
H10	0.60510	0.21490	0.20500	0.0800*
H11	0.48420	0.26180	0.04570	0.0710*
H13	0.29490	0.50300	0.16470	0.0560*
H14A	0.30240	0.30710	−0.09370	0.0750*
H14B	0.44870	0.38110	−0.09240	0.0750*
H15A	0.13040	0.42930	−0.17630	0.1250*
H15B	0.26700	0.40800	−0.23980	0.1250*
H15C	0.27350	0.50550	−0.17240	0.1250*

	U11	U22	U33	U12	U13	U23
S1	0.0391 (2)	0.0417 (2)	0.0397 (2)	0.0033 (2)	0.0004 (2)	−0.0018 (2)
O1	0.0518 (7)	0.0531 (8)	0.0479 (7)	0.0098 (6)	0.0001 (6)	0.0050 (6)
O2	0.0518 (7)	0.0455 (7)	0.0489 (7)	0.0015 (6)	0.0017 (5)	−0.0086 (5)
O3	0.0699 (9)	0.0826 (11)	0.0410 (7)	0.0166 (8)	0.0018 (6)	−0.0055 (7)
N1	0.0358 (7)	0.0540 (9)	0.0399 (8)	0.0022 (7)	0.0003 (6)	−0.0013 (7)
C1	0.0842 (17)	0.085 (2)	0.149 (3)	−0.0305 (15)	0.0439 (18)	−0.0015 (18)
C2	0.0435 (10)	0.0584 (13)	0.0886 (15)	−0.0062 (9)	0.0214 (10)	−0.0050 (11)
C3	0.0656 (12)	0.0657 (14)	0.0642 (13)	−0.0056 (11)	0.0218 (10)	0.0055 (10)
C4	0.0529 (10)	0.0608 (12)	0.0452 (10)	−0.0080 (9)	0.0060 (8)	−0.0050 (8)
C5	0.0345 (8)	0.0430 (10)	0.0457 (9)	0.0040 (7)	0.0037 (7)	−0.0041 (7)
C6	0.0475 (10)	0.0644 (13)	0.0532 (11)	−0.0058 (9)	−0.0022 (8)	−0.0056 (9)
C7	0.0462 (11)	0.0712 (15)	0.0816 (15)	−0.0128 (10)	0.0013 (10)	−0.0184 (12)
C8	0.0346 (8)	0.0438 (10)	0.0425 (9)	−0.0024 (7)	0.0069 (7)	0.0006 (7)
C9	0.0572 (11)	0.0536 (12)	0.0514 (10)	0.0122 (9)	0.0018 (9)	0.0024 (9)
C10	0.0728 (13)	0.0579 (13)	0.0669 (13)	0.0228 (11)	0.0030 (11)	−0.0065 (10)
C11	0.0590 (11)	0.0627 (13)	0.0549 (11)	0.0076 (10)	0.0076 (9)	−0.0155 (9)
C12	0.0431 (9)	0.0583 (11)	0.0428 (9)	0.0007 (8)	0.0044 (7)	−0.0032 (8)
C13	0.0441 (9)	0.0489 (10)	0.0459 (9)	0.0067 (8)	0.0049 (7)	0.0001 (8)
C14	0.0626 (12)	0.0828 (15)	0.0420 (10)	−0.0107 (11)	0.0092 (9)	−0.0129 (10)
C15	0.0858 (16)	0.116 (2)	0.0468 (12)	−0.0155 (16)	0.0038 (11)	0.0010 (13)

S1—O1	1.4245 (13)	C11—C12	1.379 (3)
S1—O2	1.4313 (13)	C12—C13	1.383 (3)
S1—N1	1.6291 (15)	C14—C15	1.500 (3)
S1—C5	1.7517 (17)	C1—H1A	0.9600
O3—C12	1.360 (2)	C1—H1B	0.9600
O3—C14	1.422 (2)	C1—H1C	0.9600
N1—C8	1.427 (2)	C3—H3	0.9300
N1—H1N	0.821 (16)	C4—H4	0.9300
C1—C2	1.501 (3)	C6—H6	0.9300
C2—C7	1.379 (3)	C7—H7	0.9300
C2—C3	1.373 (3)	C9—H9	0.9300
C3—C4	1.377 (3)	C10—H10	0.9300
C4—C5	1.375 (3)	C11—H11	0.9300
C5—C6	1.379 (3)	C13—H13	0.9300
C6—C7	1.379 (3)	C14—H14A	0.9700
C8—C13	1.374 (2)	C14—H14B	0.9700
C8—C9	1.381 (3)	C15—H15A	0.9600
C9—C10	1.374 (3)	C15—H15B	0.9600
C10—C11	1.377 (3)	C15—H15C	0.9600
S1···H13	3.0500	H1N···O2ii	2.140 (17)
S1···H10i	3.0600	H3···H1B	2.4700
O1···C13	3.019 (2)	H4···O2	2.5400
O2···N1ii	2.9476 (19)	H4···H15Bvii	2.5500
O1···H13	2.4200	H6···O1	2.6900
O1···H7iii	2.8600	H7···H1A	2.4000
O1···H10i	2.6000	H7···O1vi	2.8600
O1···H15Aiv	2.8700	H9···H1N	2.3300
O1···H6	2.6900	H9···O2ii	2.8100
O2···H4	2.5400	H10···S1viii	3.0600
O2···H11i	2.9200	H10···O1viii	2.6000
O2···H1Nii	2.140 (17)	H11···C14	2.5600
O2···H9ii	2.8100	H11···H14A	2.3000
N1···O2ii	2.9476 (19)	H11···H14B	2.4100
C6···C8	3.569 (2)	H11···O2viii	2.9200
C8···C6	3.569 (2)	H13···S1	3.0500
C13···O1	3.019 (2)	H13···O1	2.4200
C7···H14Av	3.0400	H13···H1Aiii	2.5500
C11···H14A	2.7700	H14A···C11	2.7700
C11···H14B	2.7900	H14A···H11	2.3000
C14···H11	2.5600	H14A···C7ix	3.0400
H1A···H7	2.4000	H14B···C11	2.7900
H1A···H13vi	2.5500	H14B···H11	2.4100
H1B···H3	2.4700	H15A···O1iv	2.8700
H1N···H9	2.3300	H15B···H4x	2.5500
O1—S1—O2	119.70 (8)	C2—C1—H1B	109.00
O1—S1—N1	107.95 (8)	C2—C1—H1C	109.00
O1—S1—C5	108.68 (8)	H1A—C1—H1B	109.00
O2—S1—N1	103.87 (7)	H1A—C1—H1C	109.00
O2—S1—C5	108.53 (8)	H1B—C1—H1C	110.00
N1—S1—C5	107.48 (8)	C2—C3—H3	119.00
C12—O3—C14	118.24 (16)	C4—C3—H3	119.00
S1—N1—C8	125.00 (11)	C3—C4—H4	120.00
C8—N1—H1N	116.6 (12)	C5—C4—H4	120.00
S1—N1—H1N	106.5 (12)	C5—C6—H6	121.00
C1—C2—C7	121.2 (2)	C7—C6—H6	121.00
C3—C2—C7	118.23 (19)	C2—C7—H7	119.00
C1—C2—C3	120.6 (2)	C6—C7—H7	119.00
C2—C3—C4	121.5 (2)	C8—C9—H9	121.00
C3—C4—C5	119.36 (17)	C10—C9—H9	121.00
S1—C5—C4	119.72 (13)	C9—C10—H10	119.00
C4—C5—C6	120.44 (17)	C11—C10—H10	119.00
S1—C5—C6	119.81 (14)	C10—C11—H11	120.00
C5—C6—C7	118.99 (19)	C12—C11—H11	121.00
C2—C7—C6	121.5 (2)	C8—C13—H13	120.00
N1—C8—C9	117.35 (15)	C12—C13—H13	120.00
N1—C8—C13	121.82 (15)	O3—C14—H14A	110.00
C9—C8—C13	120.63 (16)	O3—C14—H14B	110.00
C8—C9—C10	118.64 (18)	C15—C14—H14A	110.00
C9—C10—C11	121.7 (2)	C15—C14—H14B	110.00
C10—C11—C12	118.99 (19)	H14A—C14—H14B	108.00
O3—C12—C13	114.97 (17)	C14—C15—H15A	109.00
O3—C12—C11	124.94 (17)	C14—C15—H15B	109.00
C11—C12—C13	120.09 (17)	C14—C15—H15C	109.00
C8—C13—C12	119.93 (17)	H15A—C15—H15B	110.00
O3—C14—C15	107.41 (19)	H15A—C15—H15C	109.00
C2—C1—H1A	109.00	H15B—C15—H15C	109.00
O1—S1—N1—C8	−51.29 (16)	C1—C2—C3—C4	179.04 (19)
O2—S1—N1—C8	−179.35 (14)	C2—C3—C4—C5	0.2 (3)
C5—S1—N1—C8	65.76 (16)	C3—C4—C5—C6	0.3 (3)
O1—S1—C5—C4	−147.64 (14)	C3—C4—C5—S1	−177.61 (14)
O2—S1—C5—C4	−15.96 (16)	C4—C5—C6—C7	−0.6 (3)
N1—S1—C5—C4	95.79 (15)	S1—C5—C6—C7	177.28 (14)
O1—S1—C5—C6	34.49 (16)	C5—C6—C7—C2	0.4 (3)
O2—S1—C5—C6	166.16 (14)	N1—C8—C9—C10	−174.51 (18)
N1—S1—C5—C6	−82.09 (15)	C9—C8—C13—C12	−0.6 (3)
C14—O3—C12—C13	169.88 (18)	N1—C8—C13—C12	174.16 (16)
C12—O3—C14—C15	−176.27 (18)	C13—C8—C9—C10	0.5 (3)
C14—O3—C12—C11	−9.5 (3)	C8—C9—C10—C11	0.0 (3)
S1—N1—C8—C9	−133.67 (15)	C9—C10—C11—C12	−0.4 (3)
S1—N1—C8—C13	51.4 (2)	C10—C11—C12—C13	0.3 (3)
C3—C2—C7—C6	0.1 (3)	C10—C11—C12—O3	179.66 (19)
C1—C2—C7—C6	−179.4 (2)	O3—C12—C13—C8	−179.21 (16)
C7—C2—C3—C4	−0.4 (3)	C11—C12—C13—C8	0.2 (3)

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ii	0.821 (16)	2.140 (17)	2.9476 (19)	167.9 (16)
C4—H4···O2	0.93	2.54	2.914 (2)	104
C13—H13···O1	0.93	2.42	3.019 (2)	122
C14—H14A···Cg1ix	0.97	2.90	3.752 (3)	147
C15—H15C···Cg2xi	0.96	2.96	3.763 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.821 (16)	2.140 (17)	2.9476 (19)	167.9 (16)
C4—H4⋯O2	0.93	2.54	2.914 (2)	104
C13—H13⋯O1	0.93	2.42	3.019 (2)	122
C14—H14A⋯Cg1ii	0.97	2.90	3.752 (3)	147
C15—H15C⋯Cg2iii	0.96	2.96	3.763 (3)	147

Symmetry codes: (i) ; (ii) ; (iii) .